Rags to Riches wore a crown of lilies and carnations

Oct 25, 2025 Jennifer Kelly

Rags to Riches edges Curlin in the 2007 Belmont Stakes (Photo by Coglianese Photos)

Before Rachel Alexandra brought down the house and Thorpedo Anna nearly took home the Man o’ War Cup, one filly crafted a crown of lilies and carnations—Rags to Riches. In a career that was the opposite of her name, this daughter of A.P. Indy took a distaff classic and then became the first of her kind in more than a century to pass the 'Test of a Champion.'

Bred by Stanley and Marcia Gumberg’s Skara Glen Stables, dam Better Than Honour foaled a chestnut filly on Feb. 27, 2004. Her sire was a son of Seattle Slew, 1977 Triple Crown winner, and Weekend Surprise, a stakes-winning daughter of another Triple Crown winner, Secretariat. Better Than Honour was no slouch herself: winner of the Demoiselle (G2) and daughter of Blush with Pride, 1982 Kentucky Oaks (G1) victor.

Graced with a wide white blaze and socks on her right legs, Rags to Riches stood out from the beginning, so much so that she sold for $1.9 million to Michael Tabor and Derrick Smith, two-thirds of the Coolmore partnership. They then sent her to trainer Todd Pletcher to prepare her for a racing career.

Her first start and lone race at two came in June 2006 at Churchill Downs, where she was last of 10 early before going wide to make up ground and finish fourth in the 5 1/2-furlong maiden special weight. It would be her one out-of-the-money performance in her career. Rags to Riches notched her first win in her next start, the first of her three-year-old season, this time at Santa Anita. With Garrett Gomez in the saddle, Rags to Riches cruised in third early and then went to the outside to take the lead in the stretch and stretch her advantage to six lengths at the wire.

A month later, Rags to Riches got the first of her four Grade 1 victories as she tried the Las Virgenes in just her third start. After breaking slow, Gomez skillfully moving her to the outside to find a clear route and then went wide on the far turn to make up ground in the stretch. She passed Baroness Thatcher late to win by three-quarters of a length, setting up her try in the Santa Anita Oaks (G1).

In the Santa Anita Oaks, Rags to Riches emerged as the leader of her division with her performance in the 1 1/16-mile test. Facing a short field of just four others, including Baroness Thatcher, Rags to Riches stalked the pace early, went to the outside on the backstretch and then the far turn, and then took the lead in the stretch, winging away to an easy 5 1/2-length victory.

She came to Louisville for the Kentucky Oaks (G1) as the prohibitive favorite over a full field of 14, including Dreaming of Anna, who took the previous year’s Breeders’ Cup Juvenile Fillies (G1), and fellow Pletcher trainees Octave and Cotton Blossom.

Breaking from post 11, Rags to Riches showed why she came into the distaff classic as the favorite. With Gomez again in the saddle, she lingered in fifth behind Dreaming of Anna early, went three-wide on the far turn, and took command in the stretch and drew clear to win by 4 1/4 lengths. The next day, Street Sense won the Kentucky Derby (G1), with Hard Spun in second and then Curlin in third.

A month later, Pletcher announced the filly would run in the Belmont (G1). Curlin got the win over Street Sense and Hard Spun in the Preakness (G1) and came into the 12-furlong Belmont as the favorite. Rags to Riches entered the gate as the second choice but had a bit of an advantage: her half-brother Jazil had won the race the year before, showing that dam Better Than Honour was capable of producing a classic winner.

With Garrett Gomez jumping ship to Hard Spun, John Velazquez got the nod for piloting the filly in the year’s final classic. At this point in his career, Pletcher had already won two Kentucky Oaks, the first with Ashado in 2004, but had not yet gotten a classic victory. That was about to change. Rags to Riches bobbled at the start, but Velazquez stayed a cool customer in the saddle, righting the ship and lingering in fifth behind the leaders. C.P. West took command early and slowed the pace down, with a first quarter in :24.74 and then the half mile in :50.14.

As she went four wide out of the sweeping far turn, Rags to Riches had Hard Spun, Curlin, and a faltering C.P. West to her inside. Coming into the stretch, the blaze-faced filly and the Preakness victor hooked up, battling head-to-head for the final quarter. Each time she gained the minutest of advantages, he was again right there. But she was able to hold him off and win the 139th Belmont by a head, the first filly to win the race in over a century and the lone filly ever to win the Kentucky Oaks and that classic. Todd Pletcher got his first Triple Crown race win thanks to his regal distaffer.

Rags to Riches finished second in her next start, the Gazelle (G1) at Belmont Park, and emerged from the race with a hairline fracture to her right front pastern. The injury sidelined her until the following spring, when she attempted a return to training. However, she re-injured that pastern and then was retired for good. The A.P. Indy filly left the racetrack with a record of 7-5-1-0 and $1,342,528 in purses.

Though injury cut short a brilliant career, Rags to Riches remains a superstar in racing’s recent memory, a winner under the Twin Spires and conqueror of Curlin. Her place in the sport’s history earned her the namesake stakes race that is part of the Road to the Kentucky Oaks, a celebration of the potential of another generation of fillies perhaps destined to follow in her hoofprints and wear a crown of lilies and carnations of their own.